Reaction between an amino acid and ethanoyl chloride

doogleboy

If an amino acid with a -COOH group, an -OH group and an -NH2 group, would the acid chloride react with all 3 groups?

Reply 1

doogleboy

I'm thinking it would react with -OH group and -NH2 group but not the -COOH group. Would anyone like to help me???

Reply 2

*Emily*

with OH to make an ester, and with NH2 in condensation reaction, but i dont think so with the COOH (at least we havent learnt anything about it so far if it does)

Reply 3

doogleboy

That's what I was thinking, thanks. It would give an ester with the OH and a substituted amide with the NH2.

Reply 4

sea tea

it would probably substitute more than once onto the -NH₂.

Reply 5

mysteryman

It would react with all, including the COOH group. HCl is removed to give a ester bond formed.

Reply 6

mizfissy815

I don’t think the -COOH group will react. However, the –NH₂ will react with the acid chloride to form a substituted amide + HCl. The COOH group will remain it its place, unchanged.

Reply 7

sea tea

it won't react with the -COOH, it will substitute twice onto the -NH₂, and it will give an ester with the -OH, losing HCl three times.

Reply 8

*Emily*

mysteryman

It would react with all, including the COOH group. HCl is removed to give a ester bond formed.

but there would be C=O bond on either side of the oxygen joining together, so it wouldnt be an ester bond, could possibly be an anhydride or whatever they're called?

Reply 9

sea tea

wouldn't happen, you need a strong dehydrating agent like P₂O₅ to for anhydrides.

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